A convenient and rapid method for the selective oxygen-17 enrichment of aspartyl peptides during solid-phase synthesis

Vassiliki Theodorou-Kassioumis, Nikolaos Biris, Constantinos Sakarellos, Vassilios Tsikaris

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Abstract

In this work we describe, for the first time, a rapid and efficient method for 17O selective labeling on the β-carboxyl group of an aspartic acid residue already incorporated into a peptide sequence anchored on a solid-phase support. The β-O-benzyl ester of the Asp residue of the Ac-RGD-benzydrylamine resin was successfully saponified using Na17OH in a methanol/dichloromethane mixture. The 17O selective enriched peptide was then released from the solid support by acidic cleavage. The 17O NMR spectrum confirmed the 17O labeling of the Asp β-carboxylate.

Original languageEnglish (US)
Pages (from-to)7703-7705
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number43
DOIs
Publication statusPublished - Oct 22 2001

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Keywords

  • Aspartic acid
  • Isotopic enrichment
  • O NMR
  • Oxygen-17
  • RGD peptides
  • Solid-phase O peptide enrichment

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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